Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
  • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
  • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
  • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
  • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/04—Indoles; Hydrogenated indoles
  • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
  • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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  • C07D209/56—Ring systems containing three or more rings
  • C07D209/58—[b]- or [c]-condensed
  • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
• • C—CHEMISTRY; METALLURGY
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
  • C07D213/46—Oxygen atoms
  • C07D213/50—Ketonic radicals
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
  • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
  • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B45/00—Complex metal compounds of azo dyes
  • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
  • C09B45/14—Monoazo compounds
  • C09B45/20—Monoazo compounds containing cobalt
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
  • G11B7/2498—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as cations
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
  • G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
  • G11B7/2492—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds neutral compounds
• • G—PHYSICS
  • G11—INFORMATION STORAGE
  • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
  • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
  • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
  • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
  • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
  • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
  • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
  • G11B7/2495—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as anions

Definitions

• the present invention relates to an optical recording material used for an optical recording medium, in which information provided as information patterns by means of a laser and the like is recorded. More particularly, the present invention relates to an optical recording material used for an optical recording medium which is capable of high-density optical recording and reproduction by a laser of a wavelength in ultraviolet and visible regions, and of low energy, and the like, and also relates to a novel chalcone type compound and a novel metal complex comprising the compound as a ligand suitable for the optical recording material.
• optical recording media are in widespread use, generally due to its superior characteristics such as large recording capacities, non-contact recording or reproduction, and the like.
• recording is carried out by focusing the laser light on a minute area of the recording layer to change properties of the optical recording layer, while reproduction is performed based on a difference in intensities of light reflected from the recorded area and non-recorded area.
• the wavelength of a semiconductor laser used for recording and reproduction is between 750 and 830 nm for CD-R and between 620 and 690 nm for DVD-R.
• an optical disc which uses short-wavelength laser light is being explored. For example, one which uses light of wavelength between 380 and 420 nm as the recording light is under study.
• Patent Document 1 reports an optical information recording medium comprising a metal complex containing a chalcone type compound as a ligand and Patent Document 2 reports an optical recording medium comprising a specific chalcone type compound.
• Patent Document 2 reports an optical recording medium comprising a specific chalcone type compound.
• these compounds used for an optical recording medium did not necessarily have absorption wavelength characteristics suitable for an optical recording material used to form an optical recording layer.
• Patent Document 3 reports a light absorber for clothing material and, as an example of a compound used suitably as the light absorber, an organic dye compound having a chalcone type structure is cited. However, there is no description nor suggestion that the organic dye compound having the chalcone type structure may be used as an optical recording material.
• an object of the present invention is to provide an optical recording material suitable for forming an optical recording layer of an optical recording medium for short-wavelength recording light and to provide a novel compound suitable for the optical recording material.
• the present inventors conducted diligent research and, as a result, found that a specific chalcone type compound and a metal complex comprising the chalcone type compound as a ligand are suitable for forming an optical recording layer of an optical recording medium which is recorded or reproduced by short-wavelength recording light, especially laser light of wavelength between 320 and 420 nm.
• the present invention has been made based on the above findings and accomplished the above-mentioned objects by providing an optical recording material comprising a metal complex using the chalcone type compound represented by the general formula (I)as a ligand:
• rings A represents a 5- or 6-membered heterocyclic ring
• ring B represents a 5- or 6-membered heterocyclic ring, an aromatic ring, or a metallocene structure
• the heterocyclic and aromatic rings may be condensed with other rings or may be substituted.
• the present invention has accomplished the above-mentioned objects by providing an optical recording medium characterized by an optical recording layer disposed on a substrate, the recording layer formed of the optical recording material.
• the present invention provides a metal complex represented by the following general formula (VI) which is suitable as the optical recording material.
• the optical recording material of the present invention comprising at least one kind of chalcone type compound represented by the general formula (IV) or (V), the optical recording material of the invention comprising a metal complex using the chalcone type compound represented by the general formula (I), (IV) or (V) as a ligand , an optical recording medium of the invention, a novel chalcone type compound of the invention, and a novel metal complex of the invention will be described in detail based on preferable embodiments.
• optical isomers such as enatiomers, diastereomers, or a racemic mixture are present. In such a case, any optical isomer among these may be isolated and used as such or may be used as a mixture thereof in the optical recording material of the invention.
• optical isomers will not be differentiated in the present invention.
• the chalcone type compound represented by the general formula (I) will be described.
• the 5-membered heterocyclic ring represented by rings A and B includes, for example, a pyrrole, pyrazolidine, pyrazole, imidazole, imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazolidine rings, and the like;
• the 6-membered heterocyclic ring represented by rings A and B includes, for example, a piperidine, piperazine, morpholine, thiomorpholine, julolidine, pyridine, pyrazine, pyrimidine, pyridazine, triazine rings, and the like.
• the 5- or 6-membered heterocyclic ring represented by ring A as well as the 5- or 6-membered heterocyclic ring and the aromatic ring represented by rings B may be condensed with other rings or may be substituted, with examples including a quinoline, isoquinoline, indole, julolidine, naphthalene, anthracene, phenanthrene, phenylbenzene rings, and the like.
• the metallocene structure represented by ring B includes a ferrocenyl, nickelocenyl, cobaltocenyl structures, and the like. When ring B is of a metallocene structure, a carbonyl group is bonded to one of the cyclopentadiene rings of the metallocene.
• the invention provides an optical recording material comprising at least one kind of chalcone type compound represented by the general formula (IV).
• Compounds represented by the general formula (IV) are useful because they can coordinate easily with metals:
• R 16 may be the same or different and represents an alkyl groups having 1 to 8 carbon atoms which may be interrupted by -O-, -CO-, -OCO-, or -COO-, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group having 2 to 30 carbon atoms; R d , R e , and R f each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl
• chalcone type compounds represented by the general formula (IV) those having a structure represented by the following general formula (V) are useful because they can coordinate easily with metals and, by coordinating with metals, they can acquire more adequate light absorption characteristics as an optical recording material:
• R 15 may be the same or different and represents an alkyl group having 1 to 8 carbon atoms which may be interrupted by -O-, -CO-, -OCO-, or -COO-, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group having 2 to 30 carbon atoms; each of the above-mentioned alkyl group having 1 to 8 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, metallocenyl group having 10 to 30 carbon atoms, and heterocyclic
• R 16 represents an alkyl group having 1 to 8 carbon atoms which may be interrupted by -O-, -CO-, -OCO-, or -COO-, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group having 2 to 30 carbon atoms.
• the alkyl group having 1 to 8 carbon atoms includes, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, 4-cyclohexylbutyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, norbornyl, and the like; the aryl group having 6 to 30 carbon atoms includes, for example, phenyl, naphthyl, anthracen-1-yl, phenthren-1-yl, tetrac
• each of the above-mentioned groups including the alkyl group having 1 to 8 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, metallocene group having 10 to 30 carbon atoms, and heterocyclic group having 2 to 30 carbon atoms may have a substituent.
• the substituent includes the following with a note that the total number of carbon atoms possessed by R 16 satisfies the ranges specified above.
• the substituent includes, for example, an alkyl group such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, and the like; an alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy
• R d , R e , and R f represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group containing 2 to 30 carbon atoms.
• the groups represented by R d , R e , and R f namely an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a heterocyclic group containing 2 to 30 carbon atoms, and a halogen atom, include those exemplified in the description of R 16 .
• the alkenyl group having 2 to 8 carbon atoms includes, for example, vinyl, allyl, crotyl, dimethylallyl, 2-pentenyl, 2-hexenyl, 2-heptenyl, 2-octenyl, and the like.
• each of the above-mentioned groups including the alkyl group having 1 to 8 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, metallocenyl group having 10 to 30 carbon atoms, and heterocyclic group having 2 to 30 carbon atoms may have a substituent as with R 16 .
• the substituent includes the groups exemplified in the description of R 16 .
• the ring B 1 is a 5- or 6-membered ring, wherein the ring may be comprised of all carbon atoms or may be a heterocyclic ring.
• the ring comprised of all carbon atoms includes a cyclopentadiene or benzene ring;
• the 5-membered heterocyclic ring includes, for example, a furan, thiophene, pyrrole, pyrazolidine, pyrazole, imidazole, imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazolidine rings, and the like;
• the 6-membered heterocyclic ring includes a piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, julolidine rings, and the like.
• R 15 represents an alkyl group having 1 to 8 carbon atoms which may be interrupted by -O-, -CO-, -OCO-, or -COO-, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a metallocenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group having 2 to 30 carbon atoms.
• the alkyl group having 1 to 8 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, metallocenyl group having 10 to 30 carbon atoms, and heterocyclic group containing 2 to 30 carbon atoms include the groups exemplified in the description of R 16 .Each of these groups may be substituted and, as the substituent, those exemplified in the description of R 16 may be cited. When R 15 has a substituent, the total number of carbon atoms satisfies the ranges specified above.
• rings A represents a 5- or 6-membered heterocyclic ring and ring B represents a 5- or 6-membered heterocyclic ring, an aromatic ring, or a metallocene structure; the heterocyclic and aromatic rings may be condensed with other rings or may be substituted.
• rings A represents a 5- or 6-membered heterocyclic ring and ring B represents a 5- or 6-membered heterocyclic ring, an aromatic ring, or a metallocene structure; the heterocyclic and aromatic rings may be condensed with other rings or may be substituted.
• those represented by the general formula (IV) are preferable as the optical recording material of the present invention; among the chalcone type compounds represented by the general formula (IV), those represented by the general formula (V) are the most preferable.
• those represented by the general formulae (IV) and (V) are new compounds and include the above-mentioned compound Nos. 1 to 9, No. 11, No. 13, Nos. 16 to 25, and Nos. 27 to 40.
• the metal complex is formed with any of the chalcone type compounds represented by the general formulae (I), (IV) or (V) used as a ligand.
• the metal complex refers to a compound where at least one of the coordinating sites of the compounds represented by the general formulae (I), (IV) or (V) coordinates to a metal atom, more specifically a compound where the oxygen atom of the carbonyl group of the compounds represented by the general formula (I), (IV) or (V) and the metal binding atom contained in rings A and/or B bonds to the metal atom to form at least one chelate structure. It is also possible that each of the two cordinating sites possessed by the ligand is bonded to different metals.
• An optical recording layer comprising the metal complex in which the chalcone type compound described above is coordinated, has a merit that the light resistance of the optical recording layer is improved. Therefore, as an optical recording material, it is preferable to utilize the metal complex comprising the chalcone type compound as a ligand.
• the novel metal complex represented by the following general formula (VI), in which the chalcone type compound represented by the general formula (V) is coordinated is preferable because it has light absorption characteristics adequate for an optical recording material.
• M represents a metal atom selected from a group consisting of elements of the periodic table Groups 2, 8, 9, 10, 11, 12, and 13;
• M 1/k represents a structure where k ligands of the same kind coordinate to metal M;
• k is an integer from 2 to 4;
• An q- represents a q-valent anion; q is 1 or 2;
• p represents a coefficient to keep the charge neutral.
• the metal atom represented by M is preferably copper, nickel, cobalt, iron, or aluminum, because the complexes comprising these metals can be manufactured economically and show excellent light absorption characteristics.
• the anion represented by An q- includes, as a monovalent anion, for example, a halide ion such as a chloride, bromide, iodide, fluoride anions, and the like; an inorganic anion such as a perchlorate, chlorate, thiocyanate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate anions, and the like; an organic sulfonate anions such as a benzenesulfonate, toluenesulfonate, trifluoromethanesulfonate, diphenylamine-4-sulfonate, 2-amino-4-methyl-5-chlorobenzenesulfonate, and 2-amino-5-nitrobenzenesulfonate, and a sulfonate anion described in Japanese Patent Laid-Open Publication No.
• a halide ion such as a chlor
• an organic phosphate anions such as an octyl phosphate, dodecyl phosphate, octadecyl phosphate, phenyl phosphate, nonylphenyl phosphate, 2,2'-methylenebis(4,6-di-tert-butylphenyl) phosphonate anions, and the like; a bistrifluoromethylsulfonylimide anion; a bisperfluorobutanesulfonylimide anion; a perfluoro-4-ethylcyclohexanesulfonate anion; a tetrakis(pentafluorophenyl)borate anion; and the like.
• a divalent anion for example, a benzenedisulfonate anion, a naphthalenedisulfonate anion, and the like may be cited.
• a quencher anion which can deactivate (quench) the active molecules in the exited state and anions of metallocene compounds such as ferrocene, ruthenocene, and the like, which have an anionic group such as a carboxyl, phosphonate, and sulfonate groups on the cyclopentadienyl ring.
• the above-mentioned quencher anion includes, for example, those represented by the following general formula (A) or (B), or formula (C) or (D), or anions described in Japanese Patent Laid-Open Publication Nos. S60-234892 , H5-43814 , H5-305770 , H6-239028 , H9-309886 , H9-323478 , H10-45767 , H11-208118 , 2000-168237 , 2002-201373 , 2002-206061 , and 2005-297407 ; Japanese Patent Application Publication No. H7-96334 ; International Publication No. WO/98/29257 , and the like:
• R 9 and R 10 represent a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a -SO 2 -G group, G represents an alkyl, aryl that may be substituted with a halogen atom, dialkylamino, diarylamino, piperidino, or morpholino groups; a and b each independently represent an integer from 0 to 4; R 11 , R 12 , R 13 , and R 14 each independently represent an alkyl, alkylphenyl, alkoxyphenyl, or halogenated phenyl groups:
• the metal complex using as a ligand the chalcone type compound represented by any of the general formula (I), IV or (V) of the present invention is not particularly-restricted by the method of manufacture.
• it may be synthesized by a chelating reaction between the chalcone type compound which is the corresponding ligand and a metal compound.
• the metal salt compound used in the above-mentioned chelating reaction includes, for example, an inorganic metal salt such as a metal halide, hydroxide, sulfate, nitrate salts, and the like; an organic metal salt such as an acetate salt and the like; a metal lower alkoxide such as methoxide, ethoxide, isopropoxide, and the like; a chelate complex such as an acetylacetonate, EDTA salts, and the like.
• an inorganic metal salt such as a metal halide, hydroxide, sulfate, nitrate salts, and the like
• an organic metal salt such as an acetate salt and the like
• a metal lower alkoxide such as methoxide, ethoxide, isopropoxide, and the like
• a chelate complex such as an acetylacetonate, EDTA salts, and the like.
• chelating reaction there may be used as a reactant, as necessary, basic compounds such as sodium hydroxide, lithium hydroxide, sodium methoxide, sodium hydride, sodium amide, lithium amide, an organic amine compound, and the like.
• the optical recording material of the present invention comprises at least one kind of chalcone type compound represented by any of the general formulae (IV) or (V) or a metal complex using a chalcone type compound represented by any of the general formulae (I), (IV) or (V) as ligands, and is used as these compounds or as a mixture of these compounds with the solvent or various compounds, which will be described later.
• chalcone type compound represented by any of the general formulae (IV) or (V) as ligands
• the above-mentioned chalcone type compound or the metal complex and, if necessary, various compounds described later are dissolved in an organic solvent to prepare the optical recording material as a solution
• the organic solvent including a lower alcohol such as methanol, ethanol, and the like; an ether alcohol such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, butyl diglycol, and the like; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol, and the like; an ester such as ethyl acetate, butyl acetate, methoxyethyl acetate, and the like; an acrylic acid ester such as ethyl acrylate, butyl acrylate, and the like; fluorinated alcohols such as 2,2,3,3-tetrafluoropropanol and the like; a hydrocarbon
• the optical recording material is coated on a substrate by a wet coating method including spin coating, spraying, dipping, and the like. Other methods such as vapor deposition, sputtering, and the like may also be mentioned.
• a wet coating method including spin coating, spraying, dipping, and the like. Other methods such as vapor deposition, sputtering, and the like may also be mentioned.
• the organic solvent When the organic solvent is used, its amount is preferably such that the content of the chalcone type compound or the metal complex becomes 0.1 to 10% by mass of the optical recording material of the present invention.
• the optical recording layer is formed as a thin film and its suitable thickness is usually 0.001 to 10 ⁇ m, preferably in a range of 0.01 to 5 ⁇ m. Further, the above-mentioned optical recording layer is formed in such a way that the content of the chalcone type compound or the metal complex containing these compounds as ligands is preferably 10 to 100% by weight, especially 50 to 100% by mass, of the optical recording layer.
• the optical recording material of the present invention preferably contains the chalcone type compound represented by general formula (IV) or (V) of the present invention or the metal complex containing the chalcone type compound represented by any of the general formulae (1), (IV) or (V) as ligands in an amount of 50 to 100% by mass, based on the solid content of the optical recording material of the invention.
• the optical recording layer may contain, as necessary, a compound used for an optical recording layer such as a cyanine compound, azo compound, phthalocyanine compound, squarylium compound, and the like; a resin such as polyethylene, polyester, polystyrene, polycarbonate, and the like; a surfactant; an antistatic agent; a lubricating agent; a fire retardant; a radical trapping agent such as a hindered amine and the like; a pit formation accelerator such as a ferrocene derivative and the like; a dispersant; an antioxidant; a crosslinking agent; a light resistance improver; and the like.
• a compound used for an optical recording layer such as a cyanine compound, azo compound, phthalocyanine compound, squarylium compound, and the like
• a resin such as polyethylene, polyester, polystyrene, polycarbonate, and the like
• a surfactant an antistatic agent
• a lubricating agent such as
• the optical recording layer may contain, as a quencher for the singlet oxygen and the like, an aromatic nitroso compound, aminium compound, iminium compound, bisiminium compound, transition metal dithiol chelate compound, and the like. These various compounds are used preferably in a total amount ranging from 0 to 50% by mass in the optical recording layer. For that purpose, these other compounds are contained in the optical recording material of the present invention preferably in an amount of 0 to 50% by mass based on the solid content.
• the material used as the substrate on which such an optical recording layer is formed there is no particular restriction on the material used as the substrate on which such an optical recording layer is formed, provided that it is essentially transparent to the writing (recording) light and reading (reproducing) light, examples including resins such as poly(methyl methacrylate), poly(ethylene terephthalate), polycarbonate, and the like; glass and the like. Further, its shape is optionally selected corresponding to the application, from a tape, drum, belt, disc, and the like.
• a reflection film by means of a vapor deposition or sputtering method using gold, silver, aluminum, copper, and the like.
• Dielectric layers may be formed on one or both sides by a sputtering method, or protection layers may also be formed on one or both sides using an acrylic resin, an ultraviolet curing resin, and the like.
• the optical recording material of the present invention is suitable for an optical recording medium in which a semiconductor laser is used for recording and reproducing, especially suitable for publicly known single-, double-, or multi-layer optical discs such as CD-R, DVD ⁇ R, HD-DVD-R, BD-R, and the like, which are of a high-speed recording type.
• novel chalcone type compound of the present invention represented by the general formula (IV) may be used preferably as an optical recording material. In addition, it may also be used for an optical filter and the like.
• novel metal complex of the present invention represented by the general formula (VI) may be used preferably as an optical recording material. In addition, it may also be used for an optical filter and the like
• the present invention will be described in more detail in terms of Examples, Comparative Examples, and Evaluation Examples. However, the present invention will not be limited in any way by the following Examples and the like.
• the following Manufacturing Examples 1 to 10 show examples of manufacture of chalcone type compounds of the present invention, compound Nos. 1 to 8, No. 22, and No. 30.
• the following manufacturing examples 11 to 25 show examples of manufacture of metal complexes of the present invention, compound Nos. 43 to 57 using the compound Nos. 1 to 6 as ligands.
• the following Examples 1 to 19 show examples of preparation of optical recording materials of the present invention comprising compound Nos. 1 to 8 obtained in Manufacturing Examples 1 to 8 or compound Nos. 46 to 56 obtained in Manufacturing Examples 14 to 24.
• the Examples also show the manufacturing examples of the optical recording media of the present invention Nos. 1 to 19 using the optical recording materials.
• Comparative Example 1 shows an example of preparation of the comparative optical recording material using a chalcone type compound having a different structure from the compound of the present invention and also shows an example of manufacture of the comparative optical recording medium No. 1 using the comparative optical recording material.
• the compound Nos. 1 to 8, No. 22, and No. 30 were synthesized.
• the yields and analytical results ( ⁇ max, melting point, decomposition point, IR absorption spectrum, 1 H-NMR) are shown in [Table 1] to [Table 3]. It is noted that, in [Table 1], the decomposition point refers to the temperature in the differential thermal analysis performed at a heating rate of 10°C /min., whereat the mass of the sample begins to decrease.
• the residue was recrystallized from 137 g of toluene and dried to give crude crystals.
• the crude crystals obtained were placed in an autoclave, to which were added 0.200 mol of methyl iodide and 20 g of methanol, and the reaction was carried out at 100°C for 15 hrs. After removal of the solvent, the residue was recrystallized from a mixed solvent of ethyl acetate (100 g)/methanol (6.00 g) and dried to obtain the desired crude crystals.
• the chalcone type compounds obtained in the Manufacturing Examples 1 to 8 and the metal complexes obtained in the Manufacturing Examples 14 to 24 were each dissolved in 2,2,3,3-tetrafluoropropanol at concentrations of 1.0% by mass to obtain the optical recording materials of Examples 1 to 19 as 2,2,3,3-tetrafluoropropanol solutions.
• the optical recording material was spin coated on a polycarbonate disc substrate of 12 cm diameter, to form a 100 nm thick optical recording layer and obtain the respective optical recording media, the disc having been provided with a foundation layer (0.01 ⁇ m) by coating a titanium chelate compound (T-50: manufactured by Nippon Soda Co., Ltd.), followed by hydrolysis.
• the comparative optical recording material was prepared in a similar manner as in Examples 1 to 19 and, using the comparative optical recording material, the comparative optical recording medium was obtained:
• UV absorption spectra were measured of the optical recording media of Examples 1 to 19 and the comparative optical recording medium of Comparative Example 1. The results are shown in [Table 7]. It is noted that the absorbance ratio at 405 nm in [Table 7] refers to the relative value of the absorbance at 405 nm against the absorbance at ⁇ max in the UV spectrum.
• the optical recording media typified by optical discs
• preferable are those having adequate absorptions near the wavelength of laser light, namely those with the absorbance ratio relative to ⁇ max of 5 to 70%, more preferably 10 to 60%.
• the absorbance ratio is 5%, the sensitivity and degree of modulation are not enough.
• the absorbance ratio is 70% or higher, it is possible that an adequate degree of refletion is not obtained or that deterioration by reproducing light occurs.
• the optical recording media, comprising the optical recording layer formed of the optical recording material of the present invention have, the absorbance ratio relative to ⁇ max of 30 to 60% and are suitable as an optical recording material for the optical recording media which utilize laser light of 405 nm.
• the light resistance was evaluated of the optical recording media of Examples 9 to 11, 13, 15 to 19, and Comparative Example 1.
• each of the optical recording media was irradiated by light of 55,000 lux for 100 hrs., whereafter the residual rate of absorbance in the UV absorption spectrum at ⁇ max before the irradiation was measured.. The results are shown in [Table 8].
• the optical recording material of the present invention has a high light resistance and is suitable for formation of an optical recording layer of the optical recording medium.
• the present invention provides a chalcone type compound, a metal complex using the compound as a ligand, and an optical recording material comprising these, which are suitable for formation of an optical recording layer of an optical recording medium for short wavelength recording light.

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